3-Methyl­quinoxaline-2-carbonitrile

The molecule of the title compound, C₁₀H₇N₃, excluding the methyl H atoms, is essentially planar, the maximum deviation being 0.067 (2) Å for the C atom of the methyl group. The mol­ecular packing is made up of a network of weak hydrogen-bonding inter­actions involving all the N atoms, which stabilizes the mol­ecules in layers parallel to the ac plane. The inter­layer distance of ca 3.74 Å allows stabilization along the b axis by π–π stacking.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.124
• Data-to-parameter ratio = 69.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C8     -   C10     ..      10.17 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       6.85 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     -   C9      ..       6.95 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C10    ...       1.45 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  N1      ..       2.74 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A    ..  N2      ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  N3      ..       2.73 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  N3      ..       2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  N3      ..       3.00 Ang.
PLAT728_ALERT_1_C D-H..A  Calc      165.00, Rep      163.00 Dev...       2.00 Deg.
              C2   -H2   -N3      1.555   1.555   1.456

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Methylquinoxaline-2-carbonitrile

Crystal data

C10H7N3	Z = 2
Mr = 169.19	F(000) = 176
Triclinic, P1	Dx = 1.330 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.869 (2) Å	Cell parameters from 1572 reflections
b = 7.417 (3) Å	θ = 3.1–32.1°
c = 9.879 (5) Å	µ = 0.08 mm^−1
α = 72.37 (4)°	T = 293 K
β = 71.82 (3)°	Prism, yellow
γ = 64.29 (3)°	0.10 × 0.01 × 0.01 mm
V = 422.5 (3) Å^3

Data collection

Oxford Diffraction Model?? CCD diffractometer	2969 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2753 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.0827 pixels mm^-1	θmax = 32.1°, θmin = 3.1°
ω scans	h = −10→9
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	k = −10→10
Tmin = 0.993, Tmax = 0.997	l = −14→14
8147 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 0.82	w = 1/[σ^2(Fo^2) + (0.0679P)^2 + 0.2503P] where P = (Fo^2 + 2Fc^2)/3
8147 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. FT–IR (KBr): 2918, 2849. 2260,1458, 1779, 779 cm^-1. ¹H NMR (CDCl₃, 300 MHz): δ (p.p.m.): 8.13(m, 2H), 7.86 (m, 2H), 2.98(s, 3H).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.42655 (13)	0.26356 (11)	0.52161 (9)	0.0464 (2)
N2	0.09803 (12)	0.23709 (11)	0.42293 (8)	0.0470 (2)
C8	0.28032 (17)	0.25762 (14)	0.33625 (10)	0.0446 (3)
C6	0.07313 (16)	0.23208 (13)	0.56572 (10)	0.0417 (3)
C1	−0.11807 (17)	0.21306 (14)	0.66428 (11)	0.0527 (3)
H1	−0.2275	0.2056	0.6321	0.063*
C5	0.23836 (17)	0.24272 (13)	0.61560 (10)	0.0417 (3)
C9	0.64517 (16)	0.30293 (15)	0.27669 (10)	0.0596 (3)
H9A	0.7389	0.3112	0.3273	0.089*
H9B	0.5987	0.4269	0.2069	0.089*
H9C	0.7253	0.1898	0.2276	0.089*
C7	0.44581 (16)	0.27291 (13)	0.38361 (10)	0.0430 (3)
C2	−0.14095 (19)	0.20578 (15)	0.80703 (12)	0.0598 (3)
H2	−0.2673	0.1935	0.8728	0.072*
C4	0.20905 (18)	0.23444 (14)	0.76361 (10)	0.0540 (3)
H4	0.3167	0.2412	0.7981	0.065*
C3	0.0224 (2)	0.21649 (15)	0.85687 (12)	0.0607 (3)
H3	0.0031	0.2113	0.9552	0.073*
C10	0.30733 (18)	0.26221 (16)	0.18420 (13)	0.0579 (3)
N3	0.33425 (17)	0.26415 (16)	0.06474 (11)	0.0878 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0484 (5)	0.0479 (5)	0.0491 (6)	−0.0214 (4)	−0.0164 (4)	−0.0063 (4)
N2	0.0458 (6)	0.0515 (5)	0.0482 (6)	−0.0189 (4)	−0.0132 (4)	−0.0115 (4)
C8	0.0484 (7)	0.0480 (6)	0.0404 (7)	−0.0177 (5)	−0.0143 (5)	−0.0082 (4)
C6	0.0412 (7)	0.0415 (6)	0.0444 (7)	−0.0147 (5)	−0.0121 (5)	−0.0089 (4)
C1	0.0469 (7)	0.0619 (7)	0.0535 (7)	−0.0241 (6)	−0.0097 (5)	−0.0122 (5)
C5	0.0447 (7)	0.0403 (6)	0.0424 (7)	−0.0154 (5)	−0.0136 (5)	−0.0074 (4)
C9	0.0527 (7)	0.0639 (8)	0.0645 (8)	−0.0269 (6)	−0.0136 (6)	−0.0069 (6)
C7	0.0424 (6)	0.0435 (6)	0.0456 (7)	−0.0168 (5)	−0.0141 (5)	−0.0059 (5)
C2	0.0535 (7)	0.0617 (7)	0.0546 (8)	−0.0203 (6)	−0.0023 (6)	−0.0095 (5)
C4	0.0656 (8)	0.0577 (7)	0.0471 (7)	−0.0258 (6)	−0.0232 (6)	−0.0060 (5)
C3	0.0743 (8)	0.0656 (8)	0.0419 (6)	−0.0274 (7)	−0.0119 (6)	−0.0086 (5)
C10	0.0539 (8)	0.0737 (8)	0.0514 (8)	−0.0253 (6)	−0.0121 (6)	−0.0161 (6)
N3	0.0904 (8)	0.1267 (10)	0.0562 (7)	−0.0429 (7)	−0.0141 (6)	−0.0295 (6)

Geometric parameters (Å, º)

N1—C7	1.3110 (13)	C9—C7	1.5034 (13)
N1—C5	1.3765 (12)	C9—H9A	0.9600
N2—C8	1.3198 (12)	C9—H9B	0.9600
N2—C6	1.3579 (13)	C9—H9C	0.9600
C8—C7	1.4142 (14)	C2—C3	1.3977 (16)
C8—C10	1.4466 (16)	C2—H2	0.9300
C6—C1	1.4045 (14)	C4—C3	1.3590 (14)
C6—C5	1.4097 (13)	C4—H4	0.9300
C1—C2	1.3562 (15)	C3—H3	0.9300
C1—H1	0.9300	C10—N3	1.1327 (13)
C5—C4	1.3982 (14)
C7—N1—C5	117.17 (9)	C7—C9—H9C	109.5
C8—N2—C6	116.08 (10)	H9A—C9—H9C	109.5
N2—C8—C7	124.16 (9)	H9B—C9—H9C	109.5
N2—C8—C10	116.11 (11)	N1—C7—C8	120.46 (9)
C7—C8—C10	119.73 (9)	N1—C7—C9	118.84 (11)
N2—C6—C1	119.32 (11)	C8—C7—C9	120.70 (9)
N2—C6—C5	120.63 (9)	C1—C2—C3	121.03 (11)
C1—C6—C5	120.05 (10)	C1—C2—H2	119.5
C2—C1—C6	119.08 (11)	C3—C2—H2	119.5
C2—C1—H1	120.5	C3—C4—C5	119.67 (12)
C6—C1—H1	120.5	C3—C4—H4	120.2
N1—C5—C4	119.30 (11)	C5—C4—H4	120.2
N1—C5—C6	121.47 (9)	C4—C3—C2	120.94 (11)
C4—C5—C6	119.23 (10)	C4—C3—H3	119.5
C7—C9—H9A	109.5	C2—C3—H3	119.5
C7—C9—H9B	109.5	N3—C10—C8	178.22 (13)
H9A—C9—H9B	109.5
C6—N2—C8—C7	0.37 (13)	C5—N1—C7—C8	−1.28 (12)
C6—N2—C8—C10	179.78 (8)	C5—N1—C7—C9	177.92 (8)
C8—N2—C6—C1	179.23 (9)	N2—C8—C7—N1	1.20 (14)
C8—N2—C6—C5	−1.72 (12)	C10—C8—C7—N1	−178.18 (9)
N2—C6—C1—C2	179.25 (9)	N2—C8—C7—C9	−177.98 (9)
C5—C6—C1—C2	0.19 (14)	C10—C8—C7—C9	2.64 (13)
C7—N1—C5—C4	−179.26 (9)	C6—C1—C2—C3	−0.13 (15)
C7—N1—C5—C6	−0.07 (12)	N1—C5—C4—C3	179.16 (9)
N2—C6—C5—N1	1.65 (13)	C6—C5—C4—C3	−0.05 (14)
C1—C6—C5—N1	−179.30 (9)	C5—C4—C3—C2	0.12 (15)
N2—C6—C5—C4	−179.15 (8)	C1—C2—C3—C4	−0.03 (16)
C1—C6—C5—C4	−0.10 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1^i	0.93	2.74	3.651 (4)	169
C9—H9A···N2^ii	0.96	2.69	3.616 (4)	162
C2—H2···N3^iii	0.93	2.73	3.639 (4)	163
C4—H4···N3^iv	0.93	2.72	3.435 (2)	133
C3—H3···N3^iv	0.93	3.00	3.574 (2)	120

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x−1, y, z+1; (iv) x, y, z+1.